Two-Step Substitution Reaction of Phosphonates Carrying a Binaphthyl Group with Grignard Reagents Leading to the Formation of P-Chirogenic Phosphine Oxides

Shunya Ono; Aya Sugiyama; Nao Sakamoto; Kazuma Kuwabara; Mao Minoura; Toshiaki Murai

doi:10.1055/a-1979-6245

Synlett, Table of Contents

Synlett 2023; 34(12): 1502-1506
DOI: 10.1055/a-1979-6245

cluster

Special Issue Honoring Masahiro Murakami’s Contributions to Science

Two-Step Substitution Reaction of Phosphonates Carrying a Binaphthyl Group with Grignard Reagents Leading to the Formation of P-Chirogenic Phosphine Oxides

Shunya Ono

^aDepartment of Chemistry and Biomolecular Science, Faculty of Engineering, Gifu University, Yanagido, Gifu 501-1193, Japan

,

Aya Sugiyama

^aDepartment of Chemistry and Biomolecular Science, Faculty of Engineering, Gifu University, Yanagido, Gifu 501-1193, Japan

,

Nao Sakamoto

^aDepartment of Chemistry and Biomolecular Science, Faculty of Engineering, Gifu University, Yanagido, Gifu 501-1193, Japan

,

Kazuma Kuwabara

^aDepartment of Chemistry and Biomolecular Science, Faculty of Engineering, Gifu University, Yanagido, Gifu 501-1193, Japan

,

Mao Minoura

^bDepartment of Chemistry, Graduate School of Science, Rikkyo University, Nishi-ikebukuro, Toshima-ku, Tokyo, 171-8501, Japan

,

Toshiaki Murai∗

^aDepartment of Chemistry and Biomolecular Science, Faculty of Engineering, Gifu University, Yanagido, Gifu 501-1193, Japan

› Author Affiliations

Abstract

All articles of this category

This paper is dedicated to Professor Masahiro Murakami for his contribution to science.

Abstract

The reaction of phosphonates carrying a binaphthyl group with a range of Grignard reagents was complete within two hours at 0 °C to give phosphinates carrying a hydroxybinaphthyl group with high efficiency and diastereoselectivity. The resulting phosphinates were further subjected to a substitution reaction with MeMgBr. The reaction at reflux temperature in THF or toluene permitted the formation of P-chirogenic tertiary phosphine oxides with a high enantiomeric ratio. Rare examples of P-chirogenic alkynyl phosphine oxides were also obtained. The sequential one-pot substitution reaction of phosphonates bearing a binaphthyl group with two different Grignard reagents successfully gave the corresponding P-chirogenic phosphine oxides with enantiomeric ratios nearly equal to those of oxides derived from two-step reactions.

Key words

chirogenic compounds - phosphine oxides - binaphthyl phosphonates - chirality transfer reaction - one-pot reaction

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References

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13 2′-Hydroxy-1,1′-binaphthalen-2-yl phosphinates 2a–i; General Procedure A dry two-necked round-bottomed flask equipped with a magnetic stirrer bar was charged with a solution of phosphonate 1 (1 equiv) in anhyd THF under an argon atmosphere. The solution was cooled to 0 °C and the appropriate Grignard reagent (1.1 equiv) was added dropwise over 10 min, and the solution was stirred at 0 °C for a further 30 min. The reaction was then quenched with sat. aq NH₄Cl, and the mixture was extracted with Et₂O (×3). The combined organic layer was washed with H₂O, dried (MgSO₄), filtered, and concentrated. The crude product was purified by column chromatography (silica gel, hexane–EtOAc). (S_ax ,R _P)-2′-Hydroxy-1,1′-binaphthalen-2-yl ethyl(phenyl)phos-phinate [(S_ax ,R _P)-2c] White solid; yield: 1.14 g (74%); mp 196–200 °C. ¹H NMR (CDCl₃): δ = 0.79 (dt, J = 7.6, 7.6, 19.3 Hz, 3 H), 1.57–1.82 (m, 2 H), 5.05 (br, OH, 1 H), 7.1 (d, J = 8.1 Hz, 1 H), 7.17–7.34 (m, 9 H), 7.37–7.41 (m, 1 H), 7.43–7.47 (m, 1 H), 7.75–7.80 (m, 2 H), 7.76 (d, J = 9.0 Hz, 1 H), 7.91 (d, J = 8.1 Hz, 1 H), 7.98 (d, J = 9.0 Hz, 1 H). ¹³C NMR (CDCl₃): δ = 5.6 (d, ² J_C _–P = 4.7 Hz, CH₃), 23.6 (d, ¹ J_C _–P = 97.7 Hz, CH₂), 115.4, 118.8, 120.7, 120.8, 121.6, 123.4, 124.7, 125.5, 125.6, 126.5, 127.4, 127.9, 128.2, 128.3, 129.0, 129.4 (d, ¹ J_C _–P = 128.8 Hz), 130.0, 130.1, 130.7, 130.9, 131.2, 132.1, 133.5, 147.9, 147.9, 151.9. ³¹P NMR (CDCl₃): δ = 48.7 (s). MS (EI): m/z = 438 (M⁺). HRMS (EI): m/z [M⁺] calcd for C₂₈H₂₃O₃P: 438.1385; found: 438.1387.
14 CCDC 2209996 and 2209934 contain the supplementary crystallographic data for compounds (ax,R P)-S 2c and -2g, respectively. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/structures
15 (R _P)-Ethyl(methyl)phenylphosphine Oxide [(R _P)-3a]^9a; Typical Procedure A two-necked flask was charged with (S_ax )- 2c (0.088 g, 0.2 mmol) and anhyd THF (1.2 mL), and the solution was warmed to 65 °C. M A 3.0 M solution of MeMgBr in THF (0.15 mL, 0.44 mmol) was added dropwise over 15 min, and the mixture was then stirred for 1 h. Sat. aq NH₄Cl aqueous was added and the mixture was extracted with CH₂Cl₂ (×3). The combined organic layer was dried (MgSO₄), filtered, and concentrated. The crude product was purified by column chromatography on [silica gel, CH₂Cl₂–MeOH (19:1)] to give a colorless liquid; yield: 0.030 g (88%). R_f = 0.4 (CH₂Cl₂–MeOH, 19:1); [α]_D ²⁵ 0.20 (c = 1.00, MeOH). Chiral HPLC (Chiralpack IH, hexane–i-PrOH 8:2, 1 mL/min): R _t = 8.10 min. ¹H NMR (CDCl₃): δ = 1.07 (dt, J = 7.6, 7.6, 17.5 Hz, 3 H), 1.65 (d, J = 12.6 Hz, 3 H), 1.81–1.99 (m, 2 H), 7.41–7.50 (m, 3 H, Ar), 7.63–7.68 (m, 2 H, Ar). ³¹P NMR (CDCl₃): δ = 40.1 (s).

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